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Nicotinamide mononucleotide

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Nicotinamide mononucleotide
Names
IUPAC name
3-Carbamoyl-1-[5-O-(hydroxyphosphinato)-β-D-ribofuranosyl]pyridinium
Other names
  • Nicotinamide ribonucleoside 5'-phosphate
  • Nicotinamide D-ribonucleotide
  • β-Nicotinamide ribose monophosphate
  • Nicotinamide nucleotide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.851 Edit this at Wikidata
UNII
  • InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/m1/s1
    Key: DAYLJWODMCOQEW-TURQNECASA-N
  • c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)[O-])O)O)C(=O)N
Properties
C11H15N2O8P
Molar mass 334.221 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nicotinamide mononucleotide ("NMN", "NAMN", and "β-NMN") is a nucleotide derived from ribose and nicotinamide.[1] NMN is made from B vitamins in the body, and is a molecule naturally occurring in all life forms.[2] Like nicotinamide riboside, NMN is a derivative of niacin[3], and humans have enzymes that can use NMN to generate nicotinamide adenine dinucleotide (NADH).[1] In mice, NMN enters cells via the small intestines within 10 minutes converting to NAD+ through the Slc12a8 NMN transporter.[4] Because NADH is a cofactor for processes inside mitochondria, for sirtuins, and for PARP, NMN has been studied in animal models as a potential neuroprotective and anti-aging agent.[5][6] Dietary supplement companies have aggressively marketed NMN products claiming those benefits.[7] Doses of up to 500 mg was shown safe in men in a recent human study[8] at Keio University School of Medicine, Shinjuku, Tokyo Japan. Multiple long-term human studies are underway.[9] [10]

References

  1. ^ a b Bogan, KL; Brenner, C (2008). "Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition". Annual Review of Nutrition. 28: 115–30. doi:10.1146/annurev.nutr.28.061807.155443. PMID 18429699.
  2. ^ "What is NMN ?". NMN.com.{{cite web}}: CS1 maint: url-status (link)
  3. ^ "About NMN (Beta-Nicotinamide Mononucleotide)".{{cite web}}: CS1 maint: url-status (link)
  4. ^ "Slc12a8 is a nicotinamide mononucleotide transporter". Nature. January 2019.
  5. ^ Brazill, JM; Li, C; Zhu, Y; Zhai, RG (June 2017). "NMNAT: It's an NAD+ synthase… It's a chaperone… It's a neuroprotector". Current Opinion in Genetics & Development. 44: 156–162. doi:10.1016/j.gde.2017.03.014. PMC 5515290. PMID 28445802.
  6. ^ "Long-Term Administration of Nicotinamide Mononucleotide Mitigates Age-Associated Physiological Decline in Mice". Cell Metabolism. 13 December 2016.
  7. ^ Stipp, David (March 11, 2015). "Beyond Resveratrol: The Anti-Aging NAD Fad". Scientific American Blog Network.
  8. ^ "Effect of oral administration of nicotinamide mononucleotide on clinical parameters and nicotinamide metabolite levels in healthy Japanese men". Endocrine Journal. November 2019.
  9. ^ "Effect of long-term oral administration of nicotinamide mononucleotide (NMN) on human health".{{cite web}}: CS1 maint: url-status (link)
  10. ^ "Assessment of the safety of long-term nicotinamide mononucleotide (NMN)".{{cite web}}: CS1 maint: url-status (link)
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